50 Best Vacation Rentals in Sinalunga - Holiday Lettings - Cabins

Close

View larger map

Also consider

Rigomagno
19 properties
Bettolle
15 properties
Guazzino
13 properties
Farnetella
5 properties

Sinalunga

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

129 Vacation rentals

100

Vacation apartment in Guazzino

Sinalunga / Guazzino

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 90 mi
  • Child friendly
Exterior Casa Daria is a charming apartment situated in the centre of the town of Bettole, just a few kilometres from the famous Montepulciano and Cortona, in the beautiful area of the Val di Chiana in the South of Tuscany.  The apartment, which can be fo  …see more

from $59 / night

$374 - $598 / week

Inquire View

from $59 / night

(1) Excellent 

26

Vacation home in Rigomagno

Sinalunga / Rigomagno

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Part of an old farmhouse set on a hill overlooking the charming medieval village of Rigomagno and a large part of the Chiana Valley. In this area the hills are mostly covered with the silver-green foliage of olive trees, interspersed now and then with a small vineyard o  …see more

from $100 / night

$700 - $1604 / week

Book View

from $100 / night

(2) Excellent 

16

Province of Siena / Sinalunga

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 30 mi
  • Swimming pool
  • Child friendly

 …see more

from $194 / night

$1281 - $1443 / week

Book View

from $194 / night

(1) Excellent 

18

Sinalunga Vacation apartment rental

Province of Siena / Sinalunga

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
In the heart of the countryside only 40 minutes from Siena five beautiful apartments have been made by restoring an old Tuscan country house set on a hillside with views all around. Each apartment retains its fascinating original characteristics. A courtyard around the  …see more

from $110 / night

$765 - $1346 / week

Book View

from $110 / night

100

Vacation apartment in Guazzino

Sinalunga / Guazzino

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 0.3 mi
  • Child friendly
ExteriorsThe apartment is located on the second floor of a XIX century building in a small village in south Tuscany. Restaurants, Shops and Bars are at walking distance. The apartment offers a free parking space just in front of the building. High way A1 and Free Way Si  …see more

from $47 / night

$329 - $411 / week

Inquire View

from $47 / night

100

Vacation villa rental

Sinalunga / Guazzino

11 20 Min stay varies

  • 11 bedrooms
  • Sleeps 20
  • Min stay varies
  • Nearest beach 140 mi
  • Swimming pool
  • Child friendly
ExteriorsIf guests are in search of convenience and luxury, this Italian villa in Tuscany makes the perfect choice. All Tuscan and Umbrian treasures are easily accessible as this ancient 18th century residence is located nearby the highway and toll-free roads. The area  …see more

from $748 / night

$5230 - $9936 / week

Inquire View

from $748 / night

100

Villa rental in Sinalunga with swimming pool

Province of Siena / Sinalunga

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
Old stone farmhouse restored with the 1700 conservative policy that has left intact the charm and beauty of the past. Located between the Val d'Orcia and the hills of Chianti, the farmhouse is divided on two floors: on the first floor is accessed by an ancient ston  …see more

from $299 / night

$2011 - $2392 / week

Inquire View

from $299 / night

(3) Very Good 

9

Rigomagno Vacation apartment accommodation

Sinalunga / Rigomagno

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Property Description Splendid old farmhouse carefully restored to maintain its original structural features and divided into two apartments. The walls in the typical stone of this area, the ceilings in brick with wooden beams or the vaulted type of hand-made bricks, and  …see more

from $79 / night

$549 - $732 / week

Book View

from $79 / night

(1) Good 

4

Province of Siena / Sinalunga

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 25 mi
  • Swimming pool

 …see more

from $151 / night

$969 / week

Book View

from $151 / night

24

Sinalunga Vacation b&b rental

Province of Siena / Sinalunga

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The b&b is in a historic estate in the Val di Chiana, Tuscany. The first buildings date back to the twelfth century and in 1520 were executed work for the redesign of the estate, made under the direction of Baldassarre Peruzzi, who created, among others, the building of  …see more

from $103 / night

$635 - $851 / week

Book View

from $103 / night

32

Farnetella Vacation villa rental

Sinalunga / Farnetella

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Property DescriptionBeautiful and characteristic villa made of stone and bricks and completely restored to be a welcoming holiday home, situated on the green hills of the Siena countryside, 6 km far from the village of Sinalunga endowed with every kind of shops and serv  …see more

from $214 / night

$1495 - $2775 / week

Book View

from $214 / night

(1) Good 

8

Sinalunga Vacation apartment rental

Province of Siena / Sinalunga

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
In the heart of the countryside only 40 minutes from Siena five beautiful apartments have been made by restoring an old Tuscan country house set on a hillside with views all around. Each apartment retains its fascinating original characteristics. A courtyard around the  …see more

from $67 / night

$463 - $840 / week

Book View

from $67 / night

28

Sinalunga Vacation villa rental

Province of Siena / Sinalunga

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Property Description:The Agriturismo La Casetta nel Bosco is a beautiful, stone villa divided into two separate units which is part of an agritouristic Farm including olive groves, woods, several crops and a small-scale breeding of horses and ponies. The property is onl  …see more

from $153 / night

$1066 - $2067 / week

Book View

from $153 / night

25

Vacation villa with swimming pool in Rigomagno

Sinalunga / Rigomagno

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Old stone farmhouse restored with conservative criterion of 1700 that it has left intact the charm and beauty of the past. Located between the Val d'Orcia and the hills of Chianti, the farmhouse is divided on two floors: on the first floor is accessed by an ancient  …see more

from $270 / night

$1938 - $2530 / week

Book View

from $270 / night

(1) Excellent 

32

Sinalunga / Rigaiolo

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 130 mi
  • Swimming pool
  • Child friendly

 …see more

from $227 / night

$1583 - $3654 / week

Book View

from $227 / night

(5) Excellent 

41

Sinalunga / Rigomagno

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly

 …see more

from $27 / night

$189 / week

Book View

from $27 / night

25

Vacation villa with swimming pool in Sinalunga

Province of Siena / Sinalunga

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
A very attractive villa deriving from the complete refurbishment of an old country house dating from around 1800. It is situated between Sinalunga and the Parco Naturale delle Crete Senesi, in the hills covered with woods, olive groves and vineyards, at 500 metres above  …see more

from $308 / night

$2153 - $4198 / week

Book View

from $308 / night

37

Province of Siena / Sinalunga

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from $270 / night

$1884 - $2530 / week

Book View

from $270 / night

15

Vacation cottage with golf nearby in Sinalunga

Province of Siena / Sinalunga

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
This one-bedroom cottage is the perfect location for those who want to have a place to rest after a busy day spent exploring Tuscany.It consists of a living room, a double bedroom, a fully equipped kitchen with fireplace and a bathroom.The kitchen leads to a sma  …see more

from $89 / night

$508 / week

Book View

from $89 / night

7

Vacation apartment in Bettolle

Sinalunga / Bettolle

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
Ideally located between Montepulciano and Cortona in the small town of Bettolle, this holiday apartment is the perfect location to venture out and explore Tuscany. The apartment is on two levels. On the first floor there is the kitchen with a big dining table for 4 and  …see more

from $76 / night

$431 / week

Book View

from $76 / night

(1) Excellent 

28

Province of Siena / Sinalunga

1 5 3 nights min

  • 1 bedroom
  • Sleeps 5
  • 3 nights min
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly

 …see more

from $140 / night

$786 / week

Book View

from $140 / night

8

Province of Siena / Sinalunga

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from $130 / night

$754 / week

Book View

from $130 / night

(7) Very Good 

9

Vacation apartment with shared pool in Sinalunga

Province of Siena / Sinalunga

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Situated on the hills of Val di Chiana, La Giuda country farm offers an ancient stable, completely restored and furnished, divisible in three apartments in a comfortable and friendly atmosphere.The farm produces organic Chianti Classico vine and olive oil .Guest  …see more

from $140 / night

$862 / week

Book View

from $140 / night

34

Villa accommodation in Sinalunga with swimming pool, golf nearby

Province of Siena / Sinalunga

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Description:Old 18th century stone farmhouse restored following the conservation policy that has left the beauty and charm of the past intact. Located between the Val d'Orcia and the hills of the Sienese Chianti, the farmhouse is on two floors: the first floor  …see more

from $270 / night

$1884 - $2422 / week

Book View

from $270 / night

(64) Excellent 

52

Vacation villa rental

Province of Siena / Sinalunga

12 26 Min stay varies

  • 12 bedrooms
  • Sleeps 26
  • Min stay varies
  • Nearest beach 170 mi
  • Swimming pool
  • Child friendly
Villa Scopetello is the perfect holiday home for large groups and families who wish to spend their holidays together. (Between September and May it is also possible to rent just a portion of the Villa or even one bedroom) The 1000 square meter large Villa with 12 bedro  …see more

from $428 / night

$2994 - $9687 / week

Book View

from $428 / night

60

Vacation villa with swimming pool in Bettolle

Sinalunga / Bettolle

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
Originally a country estate dating back to 1795, this superb Leopoldine villa blends outstanding elegance and comfort with traditional rustic features which reflect its long history. It retains the typical rooftop pigeon-loft, now romantically transformed into an extra-  …see more

from $1320 / night

$7400 - $8745 / week

Inquire View

from $1320 / night

15

Sinalunga / Rigomagno

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from $65 / night

$377 / week

Book View

from $65 / night

11

Province of Siena / Sinalunga

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from $108 / night

$732 / week

Book View

from $108 / night

27

Province of Siena / Sinalunga

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from $162 / night

$969 / week

Book View

from $162 / night

10

Sinalunga Vacation farmhouse rental

Province of Siena / Sinalunga

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
Welcome to Villa Vignacce your holiday home in Tuscany. Villa Vignacce is located in southern Tuscany at walking distance to the Village of Bettolle. The house is divided into 5 apartments one is for me and for my dear dog Billy another one is for my son Giovanni  …see more

Pricing unknown

Book View

Pricing unknown

(1) Excellent 

101

Vacation apartment with shared pool in Guazzino

Sinalunga / Guazzino

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
A marvellous Tuscan landscape of Cortona will brighten your vacation in this comfortable and modern 810 square feet apartment. Here luxury and comfort meet Tuscan style. Originally the granary of the villa, this apartment has: a living room with a large fireplace, one r  …see more

from $107 / night

$748 - $1174 / week

Inquire View

from $107 / night

100

Guazzino Vacation apartment rental

Sinalunga / Guazzino

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
The warm color of the bedrooms, the original cow feeding basin (this used to be the barn of the villa) and the cotto floors will enchant you as soon as you step in apartment Giardino in Tuscany. The direct access to the large enclosed garden is possible through two glas  …see more

from $134 / night

$908 - $1495 / week

Inquire View

from $134 / night

(1) Excellent 

14

Province of Siena / Sinalunga

9 20 1 night min

  • 9 bedrooms
  • Sleeps 20
  • 1 night min
  • Nearest beach 200 mi

 …see more

from $87 / night

$539 / week

Book View

from $87 / night

10

Province of Siena / Sinalunga

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $323 / night

$2261 / week

Book View

from $323 / night

6

Vacation apartment in Sinalunga

Province of Siena / Sinalunga

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Private garden
Situated on the hills of Val di Chiana, La Giuda country farm offers an ancient stable, completely restored and furnished, divisible in three apartments in a comfortable and friendly atmosphere.The farm produces organic Chianti Classico vine and olive oil .Guest  …see more

from $76 / night

$485 / week

Book View

from $76 / night

17

Province of Siena / Sinalunga

3 9 3 nights min

  • 3 bedrooms
  • Sleeps 9
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from $291 / night

$2035 / week

Book View

from $291 / night

100

Guazzino Vacation apartment rental

Sinalunga / Guazzino

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
At Camino apartment you will enjoy the gentle landscape from the windows of this romantic accommodation. An 810 square feet fully-equipped apartment composed of an eat-in, fully equipped kitchen, two suites with full in-room bathrooms, and a plentiful library with  …see more

from $123 / night

$854 - $1441 / week

Inquire View

from $123 / night

20

Vacation farmhouse with swimming pool in Guazzino

Sinalunga / Guazzino

11 20 Min stay varies

  • 11 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Beautiful villa dating back to the 18th century composed by a “Leopold style” farmhouse and 3 barns accurately restored for creating a unique complex and situated on the top of a hill in absolutely quiet position with panoramic views on the surrounding countryside.  …see more

from $1014 / night

$5924 - $8874 / week

Inquire View

from $1014 / night

55

Sinalunga Vacation farmhouse rental

Province of Siena / Sinalunga

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 150 mi
  • Swimming pool
Nice farmhouse and outbuilding dating back to 17th century which have been tastefully restored preserving the ancient charm, beauty and the original architectural features like the beamed ceilings and the terracotta-tiled floors. Located between the Val d'Orcia and the  …see more

from $270 / night

$1938 - $2530 / week

Book View

from $270 / night

13

Sinalunga / Bettolle

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning

 …see more

from $92 / night

$539 / week

Book View

from $92 / night